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Acta Crystallogr Sect E Struct Rep Online. 2009 April 1; 65(Pt 4): m413–m414.
Published online 2009 March 19. doi:  10.1107/S1600536809009180
PMCID: PMC2968999

(3-Carb­oxy-5-sulfonatobenzoato-κ2 O 1,O 1′)bis­[2-(2-pyrid­yl)-1H-benzimidazole-κ2 N 2,N 3]zinc(II) monohydrate

Abstract

In the title compound, [Zn(C8H4O7S)(C12H9N3)2]·H2O, the ZnII atom has a distorted octa­hedral coordination geometry, defined by four N atoms from two 2-(2-pyrid­yl)-1H-benzimidazole ligands and two O atoms from a deprotonated carboxyl­ate group of the 3-carb­oxy-5-sulfonatobenzoate ligand. In the crystal structure, the complex mol­ecules are linked into a three-dimensional network by inter­molecular O—H(...)O and N—H(...)O hydrogen bonds, and π–π stacking inter­actions with centroid–centroid separations of 3.758 (2) and 3.597 (1) Å.

Related literature

For general background, see: Xia et al. (2005 [triangle]). For related structures, see: Kulynych & Shimizu (2002 [triangle]); Liu & Xu (2005 [triangle]); Sun et al. (2003 [triangle]); Xia et al. (2006 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-65-0m413-scheme1.jpg

Experimental

Crystal data

  • [Zn(C8H4O7S)(C12H9N3)2]·H2O
  • M r = 718.00
  • Triclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-0m413-efi1.jpg
  • a = 11.086 (4) Å
  • b = 12.695 (5) Å
  • c = 13.347 (4) Å
  • α = 63.187 (10)°
  • β = 68.376 (13)°
  • γ = 87.122 (17)°
  • V = 1543.2 (10) Å3
  • Z = 2
  • Mo Kα radiation
  • μ = 0.93 mm−1
  • T = 293 K
  • 0.14 × 0.11 × 0.08 mm

Data collection

  • Rigaku Mercury CCD diffractometer
  • Absorption correction: multi-scan (CrystalClear; Rigaku, 2002 [triangle]) T min = 0.843, T max = 0.929
  • 12166 measured reflections
  • 6935 independent reflections
  • 3857 reflections with I > 2σ(I)
  • R int = 0.035

Refinement

  • R[F 2 > 2σ(F 2)] = 0.064
  • wR(F 2) = 0.179
  • S = 0.99
  • 6935 reflections
  • 434 parameters
  • H-atom parameters constrained
  • Δρmax = 0.89 e Å−3
  • Δρmin = −0.43 e Å−3

Data collection: CrystalClear (Rigaku, 2002 [triangle]); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: SHELXTL (Sheldrick, 2008 [triangle]) and DIAMOND (Brandenburg, 1999 [triangle]); software used to prepare material for publication: SHELXL97.

Table 1
Selected bond lengths (Å)
Table 2
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809009180/hy2185sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809009180/hy2185Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Acknowledgments

This work was supported by the Natural Science Foundation of Fujian Province (grant Nos. 2006 F3141 and 2008 J0142).

supplementary crystallographic information

Comment

Increasing interest has been focused on crystal engineering of supramolecular architectures organized by coordinating covalent bonds or supramolecular contacts such as hydrogen bonding and π–π interactions (Xia et al., 2005). 5-Sulfoisophthalic acid (H3sipa), which exhibits variation in possible binding modes of the two carboxylate groups and the soft sulfonate group, and a strong tendency to form large, tightly bound metal cluster, has been demonstrated as a useful bridge ligand for the construction of supramolecular structures (Kulynych & Shimizu et al., 2002; Liu & Xu et al., 2005; Sun et al., 2003). On the other hand, 2-(2-pyridyl)-1H-benzimidazole (2-pbim) ligand presents multiple N-donor sites with the possibility of reversible protonation and deprotonation, and has the capacity to act as a donor or acceptor in the formation of multi-dimensional hydrogen bonded networks (Xia et al., 2006). We report here the crystal structure of the title compound, which contains both Hsipa and 2-pbim ligands.

As shown in Fig. 1, the title complex consists of one ZnII atom, two neutral 2-pbim ligands, one deprotonated Hsipa2- ligand and one uncoordinated water molecule. The ZnII atom is six-coordinated by four N atoms from two 2-pbim ligands and two O atoms from one carboxylate group of the Hsipa2- ligand, forming a distorted octahedral geometry (Table 1). The chelate rings A (Zn1, N1, C7, C8, N3), B (Zn1, N4, C19, C20, N6) and C (Zn1, O1, C31, O2) are oriented at dihedral angles of A/B = 84.1 (1)°, A/C = 87.8 (1)° and B/C = 82.4 (1)°. The two 2-pbim ligands bonded to the same Zn atom are nearly perpendicular to each other.

In the crystal structure, the mononuclear Zn complex molecules are linked by intermolecular O—H···O and N—H···O hydrogen bonds involving the water molecule, the imino groups, the carboxyl groups and the sulfonate group, forming a three-dimensional network (Fig. 2 and Table 2). The structure is further stabilized by π–π stacking interactions between the benzene rings of neighboring benzimidazole moieties containing N4 and N5 atoms, and between the pyridyl ring containing N3 atom and benzimidazole moiety containing N1 and N2 atoms, with centroid-to-centroid distances of 3.758 (2) and 3.597 (1) Å, respectively.

Experimental

A mixture of Zn(NO3)2.6H2O (0.092 g, 0.3 mmol), NaH2sipa (0.053 g, 0.2 mmol), 2-pbim (0.039 g, 0.2 mmol) and H2O (10 ml) was placed in a 18 ml Teflon-lined Parr acid digestion bomb. The pH value of the reaction mixture was adjusted to ca 6.0 with 10% sodium hydroxide. The mixture was then heated for 3 d at 433 K under autogeneous pressure. Slow cooling of the reaction mixture to room temperature gave colorless prism crystals (yield: ca 78% based on Zn)

Refinement

The water H atoms were located in a difference Fourier map and fixed in refinement with O—H = 0.82 Å and Uiso(H) = 1.5Ueq(O). Other H atoms were placed geometrically and refined as riding, with C—H = 0.93, O—H = 0.82 and N—H = 0.86 Å and with Uiso(H) = 1.5Ueq(O) or Uiso(H) = 1.2Ueq(C, N).

Figures

Fig. 1.
Molecular structure of the title compound. Displacement ellipsoids are drawn at the 30% probability level.
Fig. 2.
A perspective view of the crystal packing down the c axis, showing hydrogen bonds (dashed lines). H atoms, which do not participate in hydrogen bonds, have been omitted for clarity.

Crystal data

[Zn(C8H4O7S)(C12H9N3)2]·H2OZ = 2
Mr = 718.00F(000) = 736
Triclinic, P1Dx = 1.545 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 11.086 (4) ÅCell parameters from 3438 reflections
b = 12.695 (5) Åθ = 2.4–27.5°
c = 13.347 (4) ŵ = 0.93 mm1
α = 63.187 (10)°T = 293 K
β = 68.376 (13)°Prism, colorless
γ = 87.122 (17)°0.14 × 0.11 × 0.08 mm
V = 1543.2 (10) Å3

Data collection

Rigaku Mercury CCD diffractometer6935 independent reflections
Radiation source: fine-focus sealed tube3857 reflections with I > 2σ(I)
graphiteRint = 0.035
Detector resolution: 14.6306 pixels mm-1θmax = 27.4°, θmin = 2.4°
ω scansh = −13→14
Absorption correction: multi-scan (CrystalClear; Rigaku, 2002)k = −16→16
Tmin = 0.843, Tmax = 0.929l = −14→17
12166 measured reflections

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.064Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.179H-atom parameters constrained
S = 0.99w = 1/[σ2(Fo2) + (0.0855P)2] where P = (Fo2 + 2Fc2)/3
6935 reflections(Δ/σ)max < 0.001
434 parametersΔρmax = 0.89 e Å3
0 restraintsΔρmin = −0.43 e Å3

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

xyzUiso*/Ueq
Zn10.29944 (5)0.17840 (5)0.78119 (5)0.0450 (2)
S10.04872 (11)0.43789 (11)1.21208 (10)0.0462 (3)
N10.1432 (4)0.0898 (4)0.7857 (3)0.0502 (10)
N20.0072 (4)−0.0749 (4)0.8695 (4)0.0621 (11)
H2B−0.0332−0.14610.92010.075*
N30.2645 (4)−0.0040 (4)0.9412 (4)0.0541 (10)
N40.4499 (3)0.1749 (3)0.6348 (3)0.0498 (10)
N50.5526 (4)0.2558 (3)0.4336 (3)0.0522 (10)
H5B0.57710.30640.35770.063*
N60.3118 (4)0.3556 (4)0.6299 (4)0.0507 (10)
C10.0720 (5)0.1113 (5)0.7172 (4)0.0524 (12)
C20.0720 (5)0.2091 (4)0.6132 (4)0.0537 (12)
H2A0.12730.27980.57800.064*
C3−0.0115 (6)0.1981 (6)0.5644 (6)0.0768 (17)
H3A−0.01200.26310.49420.092*
C4−0.0948 (8)0.0964 (7)0.6132 (7)0.107 (2)
H4A−0.14910.09380.57510.128*
C5−0.0999 (7)−0.0010 (6)0.7164 (6)0.094 (2)
H5A−0.1585−0.06930.75060.113*
C6−0.0172 (5)0.0040 (5)0.7683 (4)0.0533 (12)
C70.1051 (4)−0.0216 (4)0.8756 (4)0.0337 (9)
C80.1661 (4)−0.0747 (4)0.9639 (4)0.0467 (11)
C90.3292 (5)−0.0428 (5)1.0183 (5)0.0565 (13)
H9A0.39840.00811.00310.068*
C100.2964 (6)−0.1531 (5)1.1166 (5)0.0701 (16)
H10A0.3428−0.17731.16700.084*
C110.1900 (6)−0.2302 (5)1.1404 (5)0.0663 (15)
H11A0.1643−0.30671.20570.080*
C120.1258 (4)−0.1844 (4)1.0597 (4)0.0489 (11)
H12A0.0539−0.23081.07260.059*
C130.5302 (4)0.0978 (4)0.6075 (5)0.0496 (11)
C140.5504 (5)−0.0146 (4)0.6844 (4)0.0529 (12)
H14A0.5075−0.04990.76870.063*
C150.6384 (5)−0.0690 (4)0.6264 (5)0.0598 (14)
H15A0.6554−0.14350.67420.072*
C160.7031 (5)−0.0199 (5)0.5016 (5)0.0694 (16)
H16A0.7606−0.06240.46840.083*
C170.6843 (5)0.0891 (5)0.4266 (5)0.0623 (14)
H17A0.72890.12290.34250.075*
C180.5970 (4)0.1477 (4)0.4791 (4)0.0408 (10)
C190.4634 (4)0.2702 (4)0.5279 (3)0.0365 (9)
C200.3960 (4)0.3701 (4)0.5214 (4)0.0494 (11)
C210.2430 (4)0.4475 (5)0.6353 (5)0.0545 (13)
H21A0.18450.43710.71100.065*
C220.2562 (5)0.5530 (5)0.5352 (5)0.0650 (15)
H22A0.20920.61380.54210.078*
C230.3456 (5)0.5667 (5)0.4189 (5)0.0713 (16)
H23A0.35800.63630.34750.086*
C240.4123 (5)0.4727 (4)0.4171 (4)0.0520 (12)
H24A0.47010.47920.34270.062*
C250.3076 (4)0.3139 (3)0.9990 (4)0.0342 (9)
C260.4187 (4)0.3155 (4)1.0245 (4)0.0365 (9)
H26A0.49350.28970.98660.044*
C270.4184 (4)0.3552 (3)1.1057 (3)0.0348 (9)
C280.3057 (4)0.3945 (4)1.1619 (3)0.0385 (10)
H28A0.30500.42191.21600.046*
C290.1968 (4)0.3927 (3)1.1374 (4)0.0374 (9)
C300.1967 (4)0.3535 (3)1.0558 (4)0.0373 (9)
H30A0.12230.35361.03910.045*
C310.3042 (4)0.2663 (4)0.9162 (4)0.0378 (9)
C320.5345 (4)0.3540 (4)1.1378 (4)0.0370 (9)
O10.1971 (3)0.2476 (3)0.9116 (3)0.0423 (7)
O1W0.8425 (3)0.3154 (3)1.1201 (3)0.0623 (9)
H1WA0.89130.36551.05160.093*
H1WB0.85530.33201.16860.093*
O20.4098 (3)0.2450 (3)0.8526 (3)0.0477 (8)
O30.5390 (3)0.3947 (3)1.2030 (3)0.0506 (8)
O40.6277 (3)0.3028 (3)1.0909 (3)0.0538 (9)
H4B0.68630.29991.11520.081*
O50.0764 (3)0.4722 (3)1.2907 (3)0.0648 (10)
O6−0.0514 (3)0.3350 (3)1.2746 (3)0.0621 (9)
O70.0208 (3)0.5357 (3)1.1155 (3)0.0687 (11)

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Zn10.0400 (3)0.0546 (3)0.0383 (3)−0.0070 (2)−0.0047 (2)−0.0269 (3)
S10.0416 (6)0.0549 (7)0.0433 (6)0.0136 (5)−0.0115 (5)−0.0285 (6)
N10.044 (2)0.060 (2)0.048 (2)0.0038 (19)−0.0146 (19)−0.028 (2)
N20.055 (2)0.059 (3)0.062 (3)−0.009 (2)−0.020 (2)−0.020 (2)
N30.045 (2)0.064 (3)0.062 (3)0.011 (2)−0.018 (2)−0.039 (2)
N40.040 (2)0.061 (2)0.046 (2)−0.0001 (19)−0.0109 (18)−0.027 (2)
N50.063 (2)0.047 (2)0.043 (2)0.0088 (19)−0.0158 (19)−0.0215 (19)
N60.045 (2)0.065 (3)0.052 (2)0.0038 (19)−0.0195 (19)−0.035 (2)
C10.047 (3)0.077 (3)0.041 (3)0.015 (3)−0.018 (2)−0.034 (3)
C20.056 (3)0.056 (3)0.043 (3)0.001 (2)−0.023 (2)−0.014 (2)
C30.075 (4)0.083 (4)0.066 (4)−0.002 (3)−0.038 (3)−0.021 (3)
C40.118 (6)0.119 (6)0.085 (5)−0.011 (5)−0.061 (5)−0.030 (5)
C50.104 (5)0.084 (5)0.099 (5)−0.008 (4)−0.064 (4)−0.025 (4)
C60.056 (3)0.059 (3)0.043 (3)0.004 (2)−0.027 (2)−0.015 (2)
C70.031 (2)0.039 (2)0.033 (2)−0.0007 (17)−0.0100 (17)−0.0193 (19)
C80.043 (3)0.050 (3)0.046 (3)0.014 (2)−0.010 (2)−0.028 (2)
C90.050 (3)0.063 (3)0.069 (3)0.016 (2)−0.040 (3)−0.027 (3)
C100.068 (4)0.071 (4)0.072 (4)0.027 (3)−0.043 (3)−0.023 (3)
C110.081 (4)0.051 (3)0.058 (3)0.022 (3)−0.023 (3)−0.023 (3)
C120.039 (2)0.059 (3)0.051 (3)0.009 (2)−0.016 (2)−0.029 (3)
C130.043 (3)0.053 (3)0.061 (3)0.002 (2)−0.019 (2)−0.033 (3)
C140.062 (3)0.041 (2)0.046 (3)0.005 (2)−0.022 (2)−0.011 (2)
C150.066 (3)0.048 (3)0.054 (3)0.009 (3)−0.022 (3)−0.016 (3)
C160.067 (3)0.065 (3)0.075 (4)0.019 (3)−0.022 (3)−0.036 (3)
C170.064 (3)0.062 (3)0.065 (3)0.016 (3)−0.017 (3)−0.040 (3)
C180.042 (2)0.044 (2)0.040 (2)0.007 (2)−0.017 (2)−0.022 (2)
C190.036 (2)0.045 (2)0.029 (2)−0.0028 (18)−0.0073 (17)−0.0207 (19)
C200.048 (3)0.058 (3)0.051 (3)0.007 (2)−0.020 (2)−0.031 (3)
C210.045 (3)0.068 (3)0.052 (3)0.022 (2)−0.015 (2)−0.034 (3)
C220.049 (3)0.068 (3)0.069 (4)0.011 (3)−0.019 (3)−0.027 (3)
C230.072 (4)0.060 (3)0.072 (4)0.011 (3)−0.032 (3)−0.019 (3)
C240.050 (3)0.064 (3)0.051 (3)0.015 (2)−0.023 (2)−0.032 (3)
C250.034 (2)0.035 (2)0.035 (2)0.0031 (17)−0.0150 (18)−0.0161 (18)
C260.035 (2)0.041 (2)0.034 (2)0.0098 (18)−0.0120 (18)−0.0193 (19)
C270.038 (2)0.037 (2)0.030 (2)0.0065 (18)−0.0163 (18)−0.0146 (18)
C280.051 (3)0.041 (2)0.031 (2)0.013 (2)−0.0198 (19)−0.0198 (19)
C290.039 (2)0.037 (2)0.036 (2)0.0081 (18)−0.0145 (19)−0.0169 (19)
C300.033 (2)0.039 (2)0.042 (2)0.0064 (18)−0.0157 (19)−0.0194 (19)
C310.043 (2)0.036 (2)0.031 (2)0.0025 (19)−0.0127 (19)−0.0139 (18)
C320.039 (2)0.042 (2)0.030 (2)0.0044 (19)−0.0171 (19)−0.0148 (19)
O10.0378 (16)0.0528 (18)0.0429 (17)0.0016 (14)−0.0164 (13)−0.0265 (15)
O1W0.0470 (19)0.079 (2)0.065 (2)0.0038 (17)−0.0263 (17)−0.033 (2)
O20.0410 (17)0.066 (2)0.0487 (18)0.0060 (15)−0.0128 (14)−0.0399 (17)
O30.061 (2)0.063 (2)0.0505 (19)0.0203 (17)−0.0378 (17)−0.0336 (17)
O40.0399 (17)0.081 (2)0.069 (2)0.0196 (17)−0.0302 (17)−0.052 (2)
O50.059 (2)0.090 (3)0.069 (2)0.0218 (19)−0.0220 (18)−0.060 (2)
O60.0487 (19)0.070 (2)0.058 (2)−0.0001 (17)−0.0080 (16)−0.0316 (19)
O70.064 (2)0.073 (2)0.055 (2)0.0364 (19)−0.0182 (18)−0.0244 (19)

Geometric parameters (Å, °)

Zn1—N12.080 (4)C11—C121.401 (7)
Zn1—N32.257 (4)C11—H11A0.9300
Zn1—N42.067 (4)C12—H12A0.9300
Zn1—N62.210 (4)C13—C141.398 (6)
Zn1—O12.216 (3)C13—C181.421 (6)
Zn1—O22.193 (3)C14—C151.373 (6)
S1—O51.431 (4)C14—H14A0.9300
S1—O71.453 (3)C15—C161.381 (7)
S1—O61.453 (4)C15—H15A0.9300
S1—C291.798 (4)C16—C171.355 (7)
N1—C71.332 (5)C16—H16A0.9300
N1—C11.348 (6)C17—C181.371 (6)
N2—C71.353 (5)C17—H17A0.9300
N2—C61.387 (6)C19—C201.423 (6)
N2—H2B0.8600C20—C241.368 (7)
N3—C81.303 (6)C21—C221.364 (7)
N3—C91.366 (6)C21—H21A0.9300
N4—C191.351 (5)C22—C231.437 (8)
N4—C131.371 (6)C22—H22A0.9300
N5—C191.367 (5)C23—C241.376 (7)
N5—C181.377 (5)C23—H23A0.9300
N5—H5B0.8600C24—H24A0.9300
N6—C201.335 (6)C25—C301.390 (5)
N6—C211.377 (6)C25—C261.397 (6)
C1—C21.384 (6)C25—C311.490 (6)
C1—C61.449 (7)C26—C271.384 (6)
C2—C31.356 (7)C26—H26A0.9300
C2—H2A0.9300C27—C281.399 (5)
C3—C41.364 (9)C27—C321.497 (5)
C3—H3A0.9300C28—C291.367 (6)
C4—C51.357 (9)C28—H28A0.9300
C4—H4A0.9300C29—C301.386 (6)
C5—C61.355 (7)C30—H30A0.9300
C5—H5A0.9300C31—O11.251 (5)
C7—C81.458 (6)C31—O21.267 (5)
C8—C121.345 (6)C32—O31.211 (5)
C9—C101.362 (7)C32—O41.306 (5)
C9—H9A0.9300O1W—H1WA0.82
C10—C111.418 (8)O1W—H1WB0.82
C10—H10A0.9300O4—H4B0.82
N4—Zn1—N1100.37 (15)C10—C11—H11A122.0
N4—Zn1—O2100.82 (13)C8—C12—C11121.3 (5)
N1—Zn1—O2156.91 (13)C8—C12—H12A119.4
N4—Zn1—N677.61 (15)C11—C12—H12A119.4
N1—Zn1—N698.96 (15)N4—C13—C14130.1 (5)
O2—Zn1—N694.45 (13)N4—C13—C18109.4 (4)
N4—Zn1—O1155.82 (14)C14—C13—C18120.5 (4)
N1—Zn1—O1101.58 (13)C15—C14—C13115.1 (4)
O2—Zn1—O159.76 (10)C15—C14—H14A122.4
N6—Zn1—O189.04 (13)C13—C14—H14A122.4
N4—Zn1—N3106.43 (14)C14—C15—C16124.1 (5)
N1—Zn1—N376.34 (16)C14—C15—H15A117.9
O2—Zn1—N388.94 (14)C16—C15—H15A117.9
N6—Zn1—N3174.19 (13)C17—C16—C15121.0 (5)
O1—Zn1—N388.58 (13)C17—C16—H16A119.5
O5—S1—O7113.4 (2)C15—C16—H16A119.5
O5—S1—O6114.6 (2)C16—C17—C18117.6 (5)
O7—S1—O6110.6 (2)C16—C17—H17A121.2
O5—S1—C29106.1 (2)C18—C17—H17A121.2
O7—S1—C29105.90 (19)C17—C18—N5133.7 (4)
O6—S1—C29105.4 (2)C17—C18—C13121.7 (4)
C7—N1—C1108.7 (4)N5—C18—C13104.6 (4)
C7—N1—Zn1113.8 (3)N4—C19—N5109.7 (4)
C1—N1—Zn1137.3 (4)N4—C19—C20122.6 (4)
C7—N2—C6108.8 (4)N5—C19—C20127.7 (4)
C7—N2—H2B125.6N6—C20—C24121.2 (4)
C6—N2—H2B125.6N6—C20—C19113.3 (4)
C8—N3—C9118.6 (4)C24—C20—C19125.5 (4)
C8—N3—Zn1114.3 (3)C22—C21—N6123.3 (4)
C9—N3—Zn1127.0 (4)C22—C21—H21A118.3
C19—N4—C13107.0 (4)N6—C21—H21A118.3
C19—N4—Zn1112.3 (3)C21—C22—C23117.5 (5)
C13—N4—Zn1139.7 (3)C21—C22—H22A121.2
C19—N5—C18109.3 (4)C23—C22—H22A121.2
C19—N5—H5B125.3C24—C23—C22117.5 (5)
C18—N5—H5B125.3C24—C23—H23A121.3
C20—N6—C21118.5 (4)C22—C23—H23A121.3
C20—N6—Zn1113.3 (3)C20—C24—C23121.9 (5)
C21—N6—Zn1128.1 (3)C20—C24—H24A119.0
N1—C1—C2133.3 (5)C23—C24—H24A119.0
N1—C1—C6108.1 (4)C30—C25—C26119.0 (4)
C2—C1—C6118.6 (4)C30—C25—C31119.7 (4)
C3—C2—C1117.6 (5)C26—C25—C31121.3 (3)
C3—C2—H2A121.2C27—C26—C25120.6 (4)
C1—C2—H2A121.2C27—C26—H26A119.7
C2—C3—C4123.3 (6)C25—C26—H26A119.7
C2—C3—H3A118.4C26—C27—C28119.5 (4)
C4—C3—H3A118.4C26—C27—C32121.7 (3)
C5—C4—C3121.2 (6)C28—C27—C32118.8 (4)
C5—C4—H4A119.4C29—C28—C27120.0 (4)
C3—C4—H4A119.4C29—C28—H28A120.0
C6—C5—C4118.3 (6)C27—C28—H28A120.0
C6—C5—H5A120.9C28—C29—C30120.8 (4)
C4—C5—H5A120.9C28—C29—S1121.1 (3)
C5—C6—N2134.9 (5)C30—C29—S1118.2 (3)
C5—C6—C1121.1 (5)C29—C30—C25120.2 (4)
N2—C6—C1104.0 (4)C29—C30—H30A119.9
N1—C7—N2110.4 (4)C25—C30—H30A119.9
N1—C7—C8122.6 (4)O1—C31—O2121.4 (4)
N2—C7—C8127.0 (4)O1—C31—C25119.3 (4)
N3—C8—C12122.8 (5)O2—C31—C25119.3 (4)
N3—C8—C7112.8 (4)O1—C31—Zn161.3 (2)
C12—C8—C7124.4 (5)O2—C31—Zn160.2 (2)
C10—C9—N3122.7 (5)C25—C31—Zn1178.0 (3)
C10—C9—H9A118.7O3—C32—O4124.1 (4)
N3—C9—H9A118.7O3—C32—C27122.6 (4)
C9—C10—C11118.6 (5)O4—C32—C27113.3 (4)
C9—C10—H10A120.7C31—O1—Zn189.1 (2)
C11—C10—H10A120.7H1WA—O1W—H1WB106.3
C12—C11—C10116.1 (5)C31—O2—Zn189.7 (3)
C12—C11—H11A122.0C32—O4—H4B109.5

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
N2—H2B···O1i0.862.152.884 (5)143
N5—H5B···O3ii0.862.052.833 (5)151
O1W—H1WA···O7iii0.821.872.678 (5)167
O1W—H1WB···O6iv0.822.052.825 (5)157
O4—H4B···O1W0.821.782.575 (4)163

Symmetry codes: (i) −x, −y, −z+2; (ii) x, y, z−1; (iii) −x+1, −y+1, −z+2; (iv) x+1, y, z.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HY2185).

References

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